Abstract
A series of organotin compounds bearing two intramolecular N → Sn coordination bonds RSn(OCH 2CH 2NMe 2) 2Cl (R = Me ( 4), n-Bu ( 5), Mes ( 6)) were synthesized in good yields. These compounds as well as 2 (R = Ph) react with PhSnCl 3 to give redistribution products RPhSnCl 2 and (Me 2NCH 2CH 2O) 2SnCl 2 ( 3). The direction of redistribution reactions is reverse to Kocheshkov reaction. DFT calculations have shown that the driving force of the reactions is formation of intramolecular N → Sn coordination bonds in (RO) 2SnCl 2 ( 3), the Lewis acid stronger than RSn(OR) 2Cl ( 2, 4– 6). The mechanism of the redistribution reaction between 2 and PhSnCl 3 consists of two steps: (1) initial exchange of OCH 2CH 2NMe 2 and Cl to give PhSn(OCH 2CH 2NMe 2)Cl 2 ( 7) followed by (2). Ph and OCH 2CH 2NMe 2 exchange.
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